N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE

Product Name: N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE
CAS No.: 216596-71-3
Chemical Name: N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE
Synonyms: C11-HSL;N-UNDECANOYL-L-HOMOSERINE LACTONE;N-[(3S)-2-oxooxolan-3-yl]undecanamide;N-undecanoyl-L-Homoserine lactone (C11-HSL);N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE;Undecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
CBNumber: CB32467468
Molecular Formula: C15H27NO3
Formula Weight: 269.38
MOL File: 216596-71-3.mol

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N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE Property

storage temp.: Store at -20°C
solubility: DMF: 20 mg/ml; DMSO: 25 mg/ml
form: A crystalline solid

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 16827
Product name: N-undecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 5mg
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 16827
Product name: N-undecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 10mg
Price: $84
Updated: 2024/03/01

Cayman Chemical

Product number: 16827
Product name: N-undecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 25mg
Price: $193
Updated: 2024/03/01

Cayman Chemical

Product number: 16827
Product name: N-undecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 50mg
Price: $299
Updated: 2024/03/01

AK Scientific

Product number: 1958AH
Product name: N-Undecanoyl-L-homoserinelactone
Packaging: 50mg
Price: $424
Updated: 2021/12/16

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N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE Chemical Properties,Usage,Production

Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C₄-C₁₈), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C₁₁-HSL possesses a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in P. aeruginosa strains.

Uses

Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial research for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C11-HSL has a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in Pseudomonas aeruginosa strains.

References

[1] MICHAIL SYRPAS. Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators.[J]. Beilstein Journal of Organic Chemistry, 2014: 2539-2549. DOI: 10.3762/bjoc.10.265
[2] SIRI RAM CHHABRA. Synthetic Analogues of the Bacterial Signal (Quorum Sensing) Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone as Immune Modulators[J]. Journal of Medicinal Chemistry, 2002, 46 1: 97-104. DOI: 10.1021/jm020909n
[3] LéA GIRARD. Characterization of N-Acyl Homoserine Lactones in Vibrio tasmaniensis LGP32 by a Biosensor-Based UHPLC-HRMS/MS Method.[J]. Sensors (Basel, Switzerland), 2017. DOI: 10.3390/s17040906

N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE Preparation Products And Raw materials

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Preparation Products

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216596-71-3, N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDERelated Search:

N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE

N-UNDECANOYL-L-HOMOSERINE LACTONE

N-[(3S)-2-oxooxolan-3-yl]undecanamide

C11-HSL

Undecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-

N-undecanoyl-L-Homoserine lactone (C11-HSL)

216596-71-3